Nitrogen → 3-(4-Hydroxybutyl)-1,8,8-trimethyl-3-azabicyclo-[3.2.1]octane-2,4-dione

HRID 1461700Notes

Reaction equation

HRID 1461700 reaction equation
N#N.[CH3:3][C:4]1([CH3:15])[C:8]2([CH3:14])[C:9]([O:11][C:12](=[O:13])[CH:5]1[CH2:6][CH2:7]2)=O.[OH:16][CH2:17][CH2:18][CH2:19][CH2:20][NH2:21].C1(C)C=CC=CC=1>O>[OH:16][CH2:17][CH2:18][CH2:19][CH2:20][N:21]1[C:12](=[O:13])[CH:5]2[C:4]([CH3:3])([CH3:15])[C:8]([CH3:14])([CH2:7][CH2:6]2)[C:9]1=[O:11]

Participants

6

Reactant 4

HCID 947NitrogenHCID 1140TolueneHCID 258684-Amino-1-butanolHCID 948341,8,8-Trimethyl-3-oxabicyclo[3.2.1]octane-2,4-dione

Product 1

HCID 146490673-(4-Hydroxybutyl)-1,8,8-trimethyl-3-azabicyclo-[3.2.1]octane-2,4-dione

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a 125 ml round-bottomed flask equipped with Dean-Stark trap, condenser, and N2 inlet were added 5.35 g (29 mmol) of d-camphoric anhydride, 2.49 g (28 mmol) of 4-hydroxybutylamine, and 60 ml of toluene. The reaction was refluxed with separation of water for 20 hours. It was then cooled, concentrated to an oil, and the oil dissolved in ethyl acetate. The ethyl acetate solution was washed with 5% HCl, 5% NaOH, and brine, dried over sodium sulfate, and evaporated to an oil, 6.0 g (85%).

Workup

  1. temperatureIt was then cooled
  2. concentrationconcentrated to an oil
  3. dissolutionthe oil dissolved in ethyl acetate
  4. washThe ethyl acetate solution was washed with 5% HCl, 5% NaOH, and brine
  5. dry with materialdried over sodium sulfate
  6. customevaporated to an oil, 6.0 g (85%)

Sources & evidence

ORD record
ord-f235a3e4cf324df5b44a3d694eb1d139
Source dataset
uspto-grants-1991_12
Patent number
US05077295

Reaction notes

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